Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis

Autores
la Venia, Agustina; Lemrová, Barbora; Krchnak, Viktor
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A protected aldehyde was attached via a twocarbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective formation of cyclic N-acyliminiums between the aldehyde and the neighboring peptide amide nitrogen. In the absence of an internal nucleophile, the cyclic iminiums formed dihydropyrazinones, a six-membered peptide backbone constraint between two peptide amides. In the presence of an internal nucleophile, tetrahydropyrazinopyrimidinediones or tetrahydroimidazopyrazinediones were formed via tandem N-acyliminium ion cyclization-nucleophilic addition. The outcome of this nucleophilic addition was dependent on the substituent on the nitrogen nucleophile.
Fil: la Venia, Agustina. Palacky University; República Checa. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Lemrová, Barbora. Palacky University; República Checa
Fil: Krchnak, Viktor. Palacky University; República Checa. University Of Notre Dame-Indiana; Estados Unidos
Materia
Iminium Chemistry
Bisheterocycles
Solid-Phase Synthesis
Regioselectivity
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/21572
Acceder
id CONICETDig_3ca98b7ee798b6dde0a0e150f23308a6
oai_identifier_str oai:ri.conicet.gov.ar:11336/21572
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesisla Venia, AgustinaLemrová, BarboraKrchnak, ViktorIminium ChemistryBisheterocyclesSolid-Phase SynthesisRegioselectivityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A protected aldehyde was attached via a twocarbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective formation of cyclic N-acyliminiums between the aldehyde and the neighboring peptide amide nitrogen. In the absence of an internal nucleophile, the cyclic iminiums formed dihydropyrazinones, a six-membered peptide backbone constraint between two peptide amides. In the presence of an internal nucleophile, tetrahydropyrazinopyrimidinediones or tetrahydroimidazopyrazinediones were formed via tandem N-acyliminium ion cyclization-nucleophilic addition. The outcome of this nucleophilic addition was dependent on the substituent on the nitrogen nucleophile.Fil: la Venia, Agustina. Palacky University; República Checa. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Lemrová, Barbora. Palacky University; República ChecaFil: Krchnak, Viktor. Palacky University; República Checa. University Of Notre Dame-Indiana; Estados UnidosAmerican Chemical Society2012-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/21572la Venia, Agustina; Lemrová, Barbora; Krchnak, Viktor; Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis; American Chemical Society; ACS Combinatorial Science; 15; 1; 12-2012; 59-722156-8952CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/co300125minfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/co300125minfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-05T09:48:39Zoai:ri.conicet.gov.ar:11336/21572instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-11-05 09:48:39.394CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis
title Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis
spellingShingle Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis
la Venia, Agustina
Iminium Chemistry
Bisheterocycles
Solid-Phase Synthesis
Regioselectivity
title_short Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis
title_full Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis
title_fullStr Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis
title_full_unstemmed Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis
title_sort Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis
dc.creator.none.fl_str_mv la Venia, Agustina
Lemrová, Barbora
Krchnak, Viktor
author la Venia, Agustina
author_facet la Venia, Agustina
Lemrová, Barbora
Krchnak, Viktor
author_role author
author2 Lemrová, Barbora
Krchnak, Viktor
author2_role author
author
dc.subject.none.fl_str_mv Iminium Chemistry
Bisheterocycles
Solid-Phase Synthesis
Regioselectivity
topic Iminium Chemistry
Bisheterocycles
Solid-Phase Synthesis
Regioselectivity
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A protected aldehyde was attached via a twocarbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective formation of cyclic N-acyliminiums between the aldehyde and the neighboring peptide amide nitrogen. In the absence of an internal nucleophile, the cyclic iminiums formed dihydropyrazinones, a six-membered peptide backbone constraint between two peptide amides. In the presence of an internal nucleophile, tetrahydropyrazinopyrimidinediones or tetrahydroimidazopyrazinediones were formed via tandem N-acyliminium ion cyclization-nucleophilic addition. The outcome of this nucleophilic addition was dependent on the substituent on the nitrogen nucleophile.
Fil: la Venia, Agustina. Palacky University; República Checa. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Lemrová, Barbora. Palacky University; República Checa
Fil: Krchnak, Viktor. Palacky University; República Checa. University Of Notre Dame-Indiana; Estados Unidos
description A protected aldehyde was attached via a twocarbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective formation of cyclic N-acyliminiums between the aldehyde and the neighboring peptide amide nitrogen. In the absence of an internal nucleophile, the cyclic iminiums formed dihydropyrazinones, a six-membered peptide backbone constraint between two peptide amides. In the presence of an internal nucleophile, tetrahydropyrazinopyrimidinediones or tetrahydroimidazopyrazinediones were formed via tandem N-acyliminium ion cyclization-nucleophilic addition. The outcome of this nucleophilic addition was dependent on the substituent on the nitrogen nucleophile.
publishDate 2012
dc.date.none.fl_str_mv 2012-12
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/21572
la Venia, Agustina; Lemrová, Barbora; Krchnak, Viktor; Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis; American Chemical Society; ACS Combinatorial Science; 15; 1; 12-2012; 59-72
2156-8952
CONICET Digital
CONICET
url http://hdl.handle.net/11336/21572
identifier_str_mv la Venia, Agustina; Lemrová, Barbora; Krchnak, Viktor; Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis; American Chemical Society; ACS Combinatorial Science; 15; 1; 12-2012; 59-72
2156-8952
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/co300125m
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/co300125m
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1847977170962481152
score 13.084122

Publicaciones similares